I'm Going On A Resort Trip With The Prez!
by KenjiMania
Summary: Issei and Rias take a holiday to Tokyo Disneyland! Fun times and awkward moments will ensue! What will our favorite perverted hero and his President do? And who decides to join them? Rated T, but could become M-Rated for the ecchiness.
1. Let's Go!

**I'm Going On A Resort Trip With The Prez!**

**A Highschool DxD Story**

**Chapter One: Let's Go!**

**Introduction:** My first story I've done in awhile. Decided to do this little ditty for Highschool DxD. I've really enjoyed the anime and have some basic knowledge of the light novels. Since it'll probably be awhile before we see another season of the show, I've decided to fast forward into the future where Issei and Rias are a couple and have been on a few dates already.

While I will write one more chapter, more can be written, depending on the response. I'm not sure how I want to do it. So, I'm counting on my readers to help dictate a continuation.

Hope you enjoy reading it.

Enjoy!

* * *

**Thursday Morning…**

**9:30am**

Issei Hyoudo looked at his reflection in his full-length mirror. He smiled as he adjusted his collar on his short sleeve shirt and made sure there were no wrinkles or stains. He ran his hands up and down the light blue shirt he wore underneath for the same reason and made sure his shoes were tied.

Taking a deep breath, he grinned and thought of how excited and nervous he was. This was his first trip with his girlfriend Rias Gremory, even during their many dates he always felt nervous and worried he might do something to ruin everything, but the joy and excitement of feeling her unbelievable body pressed against him relived him of any nervousness.

_Man, I can't wait to feel her breasts rub against my arm, chest or back!_ He grinned like his usual perverted self.

_Maybe we'll going swimming and she'll wear the skimpiest swimsuits imaginable!_ He thought, envisioning the wet body of Rias and her approaching him.

He then quickly scooped up his wallet and put it in his back pocket and slipped his watch on. He then picked up his messenger bag and grabbed his small suitcase and rolled it out. Walking out of his room and quietly shutting the door behind him, he walked down the stairs with his luggage and into the living room and saw Asia and Koneko sitting and watching the TV.

"Well, I'm leaving now." Issei told them. "I'll be home on Monday."

"Have fun. Be safe." Koneko replied with her usual stoic tone of voice as she sipped from her large glass of juice with a straw, holding the glass in both hands. The white-haired girl never took her eyes off the screen.

Asia Argento smiled and stood up from the couch and approached Issei.

"Have fun, Issei-san." She told him sweetly, her green eyes sparkling as always. She reached up with both hands and made sure to straighten his clothes out for him. "Bring me back something, please."

Issei nodded his head and grinned at the smaller girl. He pulled away and headed for the front door, as he opened it, he waved goodbye and walked out, the door shutting behind him.

Asia smiled, but a slight hint of sadness developed. "Iseei-san…. I wish we could go on a date or our own holiday." She walked back to the couch and plopped down on it. She picked up a celery stick from her plate and bit the little green piece of food.

"Someday, we will have a date or holiday with him." Koneko said again; she had placed her massive glass back down and picked up a plate that had two large sandwiches on it. She picked one up and took a big bite.

Asia stared at the girl and tilted her head to the side for a moment. She still felt a little sad, but knew that Koneko was correct in her statement. Turning back to the screen, the small blonde hoped that Issei and Rias would have fun.

* * *

Akeno Himejima stood only a few feet away from Rias, her hand folded across and in front of her as always. She smiled as she watched her friend look herself over and over again in front of the mirror. Instead of wearing her usual school outfit, Akeno wore a pink t-shirt and a pair of blue cut-off shorts.

Akeno tried not to giggle as the red-head continued to look frustrated with her look. Rias' large suitcase was next to the couch and her handbag situated on top.

"Oh my. Issei-kun should be here shortly." The vice-president told her.

Rias huffed and glared at herself and then eyed Akeno who was directly over her shoulder. She examined herself and wondered if the traditional white t-shirt and blue jeans combination was enough. She packed several clothes and other goodies as well for the 10-hour train ride to Tokyo Disneyland.

"I'm just not sure Issei will appreciate a traditional look…" Rias grumbled, she seriously thought of stripping and changing into something different for the fifth time this morning.

"Oh my. I'm sure Issei-kun will love the look." Akeno approached Rias and stood behind her now. "I know he'll be happy!"

Rias made eye contact with her longtime friend and a small smile formed. Yet, she still felt worried that he wouldn't like this, that he might expect a tight fitting tank top and form fitting jeans. She sighed loudly, before she could open her mouth again, a knock on the door stopped her.

Both beauties turned and saw Issei open the door, he looked at the two ladies and smiled broadly. Then as quickly as he entered, his eyes went wide at the sight of his two favorite girls.

_Holy shit!_ Issei thought with excitement. _Rias, Akeno, t-t-t-those outfits! OH. MY. GOD. I think I might die again!_

He stood in the doorway, clearly enamored with what he saw. Akeno simply smiled and giggled, while Rias blushed slightly.

"I-Issei?" Was all Rias could say to her boyfriend.

Issei closed his jaw and shook his head. Realizing that he was letting his perverted side out again. He bowed his head and approached the pair.

"Um, sorry for that…" He said sheepishly. He rubbed the back of his head and chuckled, he made eye contact with Akeno and then Rias.

"You look great Akeno." Issei made sure to let the raven-haired beauty know. Of course, he was doing everything in his power to not stare at her delicious breasts and that flat stomach and curves.

Akeno blushed and placed a hand on her chin in a bashful manner. "Thank you, Issei-kun." Her violet eyes scanned Issei's choice of wear and smiled. "You look quite handsome today."

"Uh, thanks…." He grinned like a goofball. Looking at Rias, he felt his heart warm up at the sight of her and realized that she looked unbelievable in her clothes.

_God, that classic look is so perfect for her!_ He thought.

"Rias…?" Issei began. She looked at him and patiently waited for his next words.

"Yes, my Issei?" Rias said sweetly.

"Y-y-you l-l-look beautiful." Issei told her nervously.

Rias blushed and a warm look developed on her face. "Thank you."

"Oh my." Akeno interrupted, she had looked at the clock and noted the time. "Your train leaves in an hour. Both of you should leave now." She explained to them politely.

Issei looked at his watch and his eyes went wide. "Yeah, we better go." He walked over and grabbed Rias' handbag and handed it to her and started to roll her large suitcase behind him. "The cab is waiting outside."

Rias slung her bag over her left shoulder and watched as Issei started to walk out. "I'll take care of your suitcase."

"Bring me back something Issei-kun!" Akeno replied waving goodbye.

"Of course." Issei replied happily. He looked at Rias as he stood in the doorway. "I'll be waiting downstairs, okay."

"Okay." Rias replied, she watched as Issei walked out and she turned to face Akeno. "Well, I'll see you on Monday."

Akeno nodded her head. "Yes, President. Have fun!" She watched as Rias walked out and shut the door behind her.

After a minute, Akeno walked towards the window and watched as Issei, with help from the driver loaded, Rias' bag into the rear of the van. As they departed and the van disappeared from view. Akeno shut the curtain and turned and snapped her fingers. Suddenly, a magic circle appeared right above and a small suitcase materialized in front of the girl.

"Oh my." Akeno pulled the handle up from her suitcase and a smaller magic circle appeared with her own handbag appearing on top of the suitcase. "Issei-kun, you didn't think that just you and Rias would be alone all weekend?"

She smiled and pulled out her train ticket. "Someone has to make sure that this weekend is more than just a fun time at the park."

While, she wasn't planning on seducing Issei too much, she still wanted to have her fun. And besides, she didn't like the idea of being alone until Monday and would miss the opportunity to spend time with her two closet and dearest friends.

As she exited out, she smiled at the thought of how happy she would be with the two of them. While also thinking of spending time with Rias and Issei and not worrying about fighting, tournaments and challenges.

Yes, this weekend was going to be fun for the three of them.

* * *

**Next:** The train ride!


	2. Riding The Train Of SelfControl

**Chapter Two: Riding The Train Of Self-Control!**

**Introduction:** Well, it certainly looks like this story is getting some love. So here's the second chapter. The third might come in a few days.

Enjoy!

* * *

**11:28AM**

They had been on the train for almost an hour now.

While the couple both lived at the Hyoudo Residence for quite awhile now. Rias did leave some of her belongings at the club room. Just in case something happened that forced her to stay at the club room. Thankfully, none of that had occurred recently. She reasoned that it would nice to spend time with Akeno before she left with Issei, hence why the night before, she slept in her old bed and let Issei pick her up there.

After they arrived at the station and passed the security checkpoints, they picked up their tickets and had their luggage taken to the luggage car, soon after, they had boarded and were now sitting at one of the many luxurious dining cars and awaiting a their lunch.

And so it was, that Issei sat across from Rias and watched as she carefully unfolded her napkin and placed the large white sheet on her lap, she rested her hands on top of said napkin and looked at Issei and smiled. She looked so cute when her eyes went wide with happiness and she smiled that smile that melted his heart and made him feel all warm and gooey.

He grinned and coughed before attempting to speak. "Um…."

"What is it my Issei?" Rias said with that cheery voice whenever she was outside of the Club room.

_Damn, her cuteness makes it so hard to talk to her…_ Issei thought. _I'd rather just stare at her all day and night!_ He stared at her with the same adoration he held for her long before they met.

Rias tilted her head to the side and her smile grew even wider. "Issei-kun?" She quietly said; she lifted a hand and reached over to gently clasp his that was resting next to the silverware. "Did you want to tell me something?"

The boy who held the Boosted Gear felt the soft skin of his Prez and looked down and watched as he held her hand and felt her thumb gently stroke his knuckles. Issei swallowed and looked up at her again.

"Well…" He tried to start the conversation over again. "I, um, wanted to say…"

The red-head simply watched as the boy she loved again struggled with forming any sort of coherence in his speech. Yet, it didn't bother her one bit as that was one of the many things she loved about him and what made her feel like a normal person not a devil or the future head of the Gremory family.

"Issei…" She said his name again; he looked up and stared into her blue-green eyes. "You can tell me anything, okay?"

He felt a small trickle of sweat move down his brow, but he quickly shook off any nervousness and breathed a small sigh to relax. Looking at Rias, Issei smiled and held her hand even tighter.

"It's so awesome that we can be alone and just be a normal couple." The brown-haired boy let out slowly.

Rias smiled and she felt her cheeks warm up. "I know." She knew how genuine his words were and how they both knew they could finally be 'normal' people, not devils or heirs. "It's so nice to be alone."

Issei nodded his head and looked out the window to his right and saw his reflection as the train moved past at high speeds towards Tokyo and to their final destination at Disneyland. He saw the peaceful scenery and a sea of green and several crystal-clear blue lakes. He noticed out of the corner of his eye that Rias was also watching the scenery too.

"I'm sorry we couldn't fly over…" Issei quietly told her as he turned his head to look at her.

Rias simply smiled and chuckled. "Don't worry, we saved all our money for this trip and could only afford a train ride." Still holding her fiancée's hand she picked up her glass of water and took a quick sip.

"Besides, we're high-schoolers," She explained, placing her glass back down, before she rationalized everything for him. "Even when we go to college, money will be tight."

Issei nodded in agreement. Deciding to move past the subject of money, he thought of all the fun that they would have together. The rides, the shows, the food and especially DisneySea and the all the fun that would come with that. He could only imagine how much enjoyment they would have this whole weekend. Of course, they decided to head to the beach first thing tomorrow morning and have some fun. Rias had told him she would wear a cute swimsuit just for him and they even agreed to try and build a sandcastle.

The swimsuit though, was all he could think about.

Quickly, lecherous thoughts formulated in his mind and he wondered if she would wear a thong or g-string. Then, he imagined the water cascading down her body as she walked out of the water and towards him. The sexy look on her face and the way her hips would swivel and the bounciness of her boobs.

He bit his lips in excitement and felt the blood throughout his body move every which way. Either to his privates, nose or head, clearly his own body didn't know what to do.

"Are you thinking perverted thoughts of me Issei-kun?" Rias interrupted while leaning closer and whispering to him. She poke her tongue out and licked her red lips quickly.

More sweat trickled down his brow and he nodded dumbly. He tried everything he could to prevent his eyes from moving lower and staring down and into her white t-shirt.

_Don't look down! Don't look down! Don't look down!_ Issei thought rapidly. Fortunately, his eyes did travel down and look down her shirt and saw his favorite part of a woman's anatomy. He saw the mounds of heaven pressed together because of her white lacey bra. His eyes went slightly wide as his mouth watered at the sight of her incredible chest.

"My cute Issei." Rias again whispered seductively, lifting a hand and placing two fingers under his chin and lifting his head up so that they made eye contact. "Your breathing is labored and your heart is beating fast."

All Issei could do at this point was just star into those beautiful blue-green eyes. He was clueless as to what to say and could only hope that he didn't do anything stupid.

"Am I that beautiful to you?" Rias asked as made a cute face. She pulled away and sat back down and waited for his response.

He nodded his head in response and instinctively picked up his glass of water and gulped down half of it. He picked up one of several napkins on the table and wiped some sweat off his brow. Closing his eyes, he took several deep breathes before finally opening his eyes again.

"Yes, you are that beautiful." He finally replied, with as much calm and self-control as possible.

Rias cheeks turned a slight shade of red at his reply. She was used too and always appreciated his compliments or kind words. Yet, she always blushed or felt her heart skip several beats at how sweet and genuine he was towards hers when they were alone. It's one of the several reasons she fell in love with him.

"Thanks." Rias said with a smile. "And you're that handsome."

"Thanks." He replied. Issei grinned sheepishly and his cheeks now turned slightly red. This time he moved his hand and gently held hers. They smiled at one another and quietly sat and enjoyed each other's company.

For the next hour as they were delivered their food; they talked about mundane topics and how much they were looking forward to this weekend getaway. After everything they had been through, they both learned, even at their young age, to appreciate the little things when it came to relationships. They knew it was these moments that brought them closer and strengthened their love for the other.

As the young couple sat, in another train car was Akeno. She was sitting inside one of the roomettes and with the curtain pulled down over the door's window. She rested on her side and watched via a magic circle the entire interaction between Issei and Rias.

The raven-haired girl smiled warmly at the sight. She felt her heart fill with happiness and watched as the two most important people in her life enjoyed their time alone. Akeno closed the image and sat up and watched the outside world move past.

"My Issei-kun…" Akeno said aloud as she sighed. She wondered if this was the right thing to do. That maybe she should have stayed and spent time with Kiba and the others. But she knew they would all be busy and that she'd alone at times.

"I just hope they don't get mad when they see me…" Akeno thought with some sadness.

She rested her elbow on the windowsill and rested her chin on her fist and watched the world pass. Wondering if she could have fun just like they would.

* * *

**Next:** Hotel Arrival!


	3. I Find Out The Reasons Why

**Chapter Three: I find out the reasons why…**

**Introduction:** It's been quite awhile. I'm amazed that you people wrote such negative reviews about the first two chapters. You know, I mentioned that I have limited knowledge of what happened in the light novels and manga when compared to the anime. I did read up on where they are in their lives after writing the first chapter and planned to write a rational explanation. I honestly thought of never finishing this story, but decided that I'll keep doing this story until I feel it's not worth writing anymore.

As a reminder, I'll do what I want with this story when it comes to honorifics and such. Unless any of you can do better, write your own. Or don't bother reading.

* * *

**7:21PM**

The sun had set almost an hour ago.

After eating lunch, Issei and Rias had retired to their roomette. They had decided to watch a movie and chose Superman/Batman: Apocalypse, after watching the movie on Rias' laptop, they grabbed a blanket and some pillows and decided to get some sleep. Deciding to save their energy fro the weekend, they decided to get some sleep. While it wasn't an overnight trip, the trip ended up being longer and was closer to 11 hours and not the original 10.

Five and half hours had passed and Issei and Rias sat in their seat snuggled together. Rias rested her head on his left shoulder, her left arm wrapped behind his lower back and her other resting on his blanket covered lap. The wielder of the Boosted Gear kept an arm wrapped around his girlfriend's shoulders and his other hand held her hand on his lap.

Even though they were traveling via train, which he still didn't quite understand why, given all the money they had, the ride was quiet and smooth and the only noise besides the incredibly low engine was the breathing of the young couple. The lights were off and the only thing that illuminated the room was the full moon.

Issei was the first to wake up. He slowly opened his eyes and the first thing he looked at was the red hair of his love. He smiled softly as he listened to her gentle breathing and felt the rise and fall of her chest, listening too how deep and spread apart her breathing was and wondered what she was dreaming.

_I wonder if she's dreaming about our wedding day…._ Issei thought to himself; knowing it was more truth than a question or fantasy. He lifted his head carefully so as not to wake her and looked outside and saw how beautiful the night was. He immediately remembered how many of his early fights were at night and how when he finally met Rias, it was in the middle of the night as he lay dying. It was a moment that he never forgot, even if it wasn't the prettiest image of his bloody and skewered body lying on the concrete, but there were time that he wondered if it was just dumb luck.

Then again, making all the money because of the television show and having a massive house to live in might be considered dumb luck. Staring outside, he saw his reflection on the window and watched as the lights of the various houses in the distance moved by. He could still make out the green of the forest and hills as the train was coming closer to their final destination.

He just didn't understand why they couldn't just jet over and why she wanted to do something so simple. He tried wrapping his brain around why she wanted this trip to be this simple.

Issei's thoughts were broken when felt a gentle stirring of Rias against him as he looked down and saw her peaceful, and gorgeous face, and how her nose was wrinkled up in such a cute manner, that he stopped breathing for a few seconds, he watched as her lovely eyes started to flutter open. She slowly pulled away from him and lifted her arms into a loud yawn, her voluptuous breasts jiggling like they always did when she woke up and yawned.

He tried everything he could to calm his body down, knowing that the blood flow would either go down to his pants or up to his nose. He tried thinking of something different, but watched as she kept her eyes shut and stretched her arms over her head and his favorite part of her kept jiggling, almost tempting him to fondle and squeeze those perfect mounds., and rest his head on top of them and fall asleep.

_Damn it, brain!_ Issei thought shutting his and eyes, her ran his hands through his brown hair roughly and shook himself. _Think of something different. Intense violence! Beatings by the kendo club! Getting punched by Motohama! Anything!_

"Good evening my cute Issei." Rias said in her ever-lovely voice. He hadn't looked at her yet, but felt the soft touch of her left hand on his thigh and her right reached up to grab one of his hands.

She slowly intertwined their fingers and watched as Issei opened his eyes and looked into the emerald orbs of the girl he loved. He swallowed a small lump in his throat and felt himself relax at her touch and loving gaze.

"Is something wrong?" His red-headed beauty asked sweetly.

"No…." Issei quietly replied without any hint of hesitation. Then he remembered what it was that he wanted to ask her. "Well, um…"

"What?" She gave his thigh a gentle squeeze, her soft expression and genuineness towards him made it easier for Issei to speak up.

He scratched the back of his head in a sheepish manner before finaly opening up. "Well, I was wondering, why you chose not to use all our money for a private jet…?" He looked at her face and noticed that she listening closely and patiently. "I mean, we're rich and can go anywhere, do anything…" He rubbed the back of his head with his free hand taking a breath.

Rias giggled for a second before smiling softly. "Issei," She began, "I love how you think money will make everything easy, but…"

She paused and snuggled closer to him, letting go of his hand that she held, she lifted her hands up and caressed his cheeks with both. Issei just stared into her impossibly beautiful face and watched as she took her own deep breath before continuing.

"I've lived my whole life in luxury and with the opportunity to have anything and everything that I want." Staring into the boy she loved in the eyes, she tilted her head to the left and looked down at the floor before looking up again and admiring into his ridiculously handsome face. "I wanted to go to Kuoh Academy so that I could experience what it's like to be a normal everyday girl. Not just Rias of the Gremory family, but just be a normal person. I'm so proud of my family and where I came from, but I just want to be a normal girl. Experience normal things in life, the daily struggles, the heartbreak and the joys that come from overcoming failures."

Issei watched as she poured her heart out to him and felt his own warm up at the reason for her wanting too not spend their fortune for this trip. He felt like an ass for thinking those things earlier, but shook away those thoughts when he understood how much she wanted to be like him before they met. Normal people living life and experiencing the best and worst that the world had to offer.

He was again reminded why he loved her and would always protect her and do everything to make her happy. He was about open his mouth to speak when she interrupted him again.

"Issei, I know that you've been a devil for a long time, yet, you are still human, and that you bring me so close to humanity." She lowered her right hand and placed her hand over his chest to feel his heartbeat. "It's why I was so afraid of losing you before," She paused and tried to hold back the tears that would come. "I would lose my only bridge to being human and never know what it's like to experience all that I have since coming to Kuoh…"

"Rias…." Issei spoke softly, he reached up and placed his hand over the one on his chest and held it. "I…" He bit his lip before he said something again. "I forget sometimes that you want to be a normal girl…" He exhaled and looked into her eyes. "That you don't want to take anything for granted…"

Rias' smile grew wider and she felt her heart beat faster, she watched as he placed his own hand on her chest and felt it beat as well. Rias then lowered her free hand and pressed his hand against her chest. They shared an intimate bond that only they understood, though maybe one other person, but at the moment they didn't care.

"I love you, Rias." Issei told her while looking into her green eyes that he adored so much. "If doing our trip this way makes you happy…" He gave her a loving gaze and a smile that would always melt her heart. "Makes me happy…"

Rias smiled and felt the tears going away replaced by the warmth that he gave her with his words. She leaned forward and pressed her forehead against his and shut her eyes. Issei shut his own eyes and smiled.

"I love you, my Issei." Rias whispered, not holding back the love in her words. "Thank you so much." They held each other for the remainder of the train ride until it reached their destination. After packing up their stuff, they walked out with their arms wrapped each other's waists.

As they stepped off the train, they walked towards where the luggage was being unloaded. They waited patiently for their names to be called to collect their belongings not aware that only a few hundred feet away was Akeno stepping off the train and watching the couple walk away with their bags.

She bit her lip and with her hands folded in front of her watched them walk towards the train station building. She sighed and went to grab her luggage thinking about how happy they were and how she hoped she could have some of that happiness as well.

As she dragged her suitcase behind her, she thought long and hard about how much she loved them both and hoped that when the inevitable did happen and they saw her, they wouldn't be too upset.

"If anything, they'd both understand." Akeno murmured to herself as she strolled into the building, dreaming of a lovely holiday for them and for her.

* * *

**Next:** The first day….


End file.
